IP Library Granted Patent US 10,020,456
Granted Patent B2
US 10,020,456 · App. 15/514,180 · Granted Jul 10, 2018

Ether-based polymers as photo-crosslinkable dielectrics

Inventors: Emmanuel Martin (Folgensbourg, FR); Fulvio G. Brunetti (Singapore, SG); Mi Zhou (Seoul, KR); Stefan Becker (Seoul, KR); Daniel Kaelblein (Mannheim, DE); Chao Wu (Mannheim, DE); Raimond Praptana (Singapore, SG); Konrad Knoll (Mannheim, DE); Jordan Thomas Kopping (Allschwil, CH)
Assignee: BASF SE
H01L51/052C08F12/32C09D125/18H01L51/004H01L51/0043
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,020,456
App. No.
15/514,180
Granted
Jul 10, 2018
Kind
B2
Abstract

Polymers comprising at least one unit of formula (1) wherein n is 0 or 1, m and p are independently from each other 0, 1, 2, 3, 4, 5 or 6, provided that the sum of n, m and p is at least 2, and n and p are not 0 at the same time, Ar 1 and Ar 2 are independently from each other C 6-14 -arylene or C 6-14 -aryl, which may be substituted with 1 to 4 substituents independently selected from the group consisting of C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl and 5 to 14 membered heteroaryl, and X 1 , X 2 and X 3 are independently from each other and at each occurrence O or S, compositions comprising these polymers, and electronic devices comprising a layer formed from the compositions. Preferably, the electronic device is an organic field effect transistor and the layer is the dielectric layer.

Claims (72)

1. A polymer, comprising:

at least one unit of formula (1):

wherein:

n is 0 or 1;

m and p are independently from each other 0, 1, 2, 3, 4, 5 or 6,

provided that the sum of n, m and p is at least 2, and n and p are not 0 at the same time;

Ar 1 and Ar 2 are independently from each other a C 6-14 -arylene or a C 6-14 -aryl, which may be substituted with 1 to 4 substituents independently selected from the group consisting of a C 1-30 -alkyl, a C 2-30 -alkenyl, a C 2-30 -alkynyl, a C 5-8 -cycloalkyl, a C 6-14 -aryl and a 5 to 14 membered heteroaryl;

X 1 , X 2 and X 3 are independently from each other and at each occurrence O or S;

R 1 and R 2 are independently from each other and at each occurrence selected from the group consisting of a C 1-30 -alkyl, a C 2-30 -alkenyl, a C 2-30 -alkynyl, a C 5-8 -cycloalkyl, a C 6-14 -aryl and a 5 to 14 membered heteroaryl;

C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 5-6 -cycloalkyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl;

C 5-8 -cycloalkyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, a C 1-10 -alkyl, CN, a C 2-10 -alkenyl, a C 2-10 -alkynyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl; and

C 6-14 -aryl and 5 to 14 membered heteroaryl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 1-10 -alkyl, a C 2-10 -alkenyl, a C 2-10 -alkynyl and a C 5-6 -cycloalkyl.

2. The polymer of claim 1 , wherein:

n is 0 or 1; and

m and p are independently from each other 0, 1, 2, 3 or 4,

provided that the sum of n, m and p is at least 2, and n and p are not 0 at the same time.

3. The polymer of claim 1 , wherein:

n is 0 or 1; and

m and p are independently from each other 0, 1, 2, 3 or 4,

provided that the sum of n and p is at least 2.

4. The polymer of claim 1 , wherein:

n is 0 or 1; and

m and p are independently from each other 0, 1, 2, 3 or 4,

provided that the sum of n and p is at least 3.

5. The polymer of claim 1 , wherein:

Ar 1 and Ar 2 are independently from each other a phenylene or phenyl, which may be substituted with 1 to 4 substituents independently selected from the group consisting of a C 1-30 -alkyl, a C 2-30 -alkenyl, a C 2-30 -alkynyl, a C 5-8 -cycloalkyl, a C 6-14 -aryl and a 5 to 14 membered heteroaryl;

C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 5-6 -cycloalkyl, a C 6-10 -aryl, and a 5 to 10 membered heteroaryl;

C 5-8 -cycloalkyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 1-10 -alkyl, a C 2-10 -alkenyl, a C 2-10 -alkynyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl; and

C 6-14 -aryl and 5 to 14 membered heteroaryl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 1-10 -alkyl, a C 2-10 -alkenyl, a C 2-10 -alkynyl and a C 5-6- cycloalkyl.

6. The polymer of claim 1 , wherein:

Ar 1 and Ar 2 are independently from each other a phenylene or phenyl, which may be substituted with 1 to 4 substituents independently selected from the group consisting of a C 1-20 -alkyl, a C 2-20 -alkenyl and a C 2-20 -alkynyl; and

C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 5-6 -cycloalkyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl.

7. The polymer of claim 1 , wherein Ar 1 and Ar 2 are independently from each other an unsubstituted phenylene or phenyl.

8. The polymer of claim 1 , wherein:

at least one of n, m and p is not 0, and

X 1 , X 2 and X 3 are 0.

9. The polymer of claim 1 , wherein:

R 1 and R 2 are independently from each other and at each occurrence selected from the group consisting of a C 1-20 -alkyl, a C 2-20 -alkenyl, a C 2-20 -alkynyl and phenyl;

C 1-20 -alkyl, C 2-20 -alkenyl and C 2-20 -alkynyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 5-6 -cycloalkyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl; and

phenyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 1-10 -alkyl, a C 2-10 -alkenyl, a C 2-10 -alkynyl and a C 5-6 -cycloalkyl.

10. The polymer of claim 1 , wherein:

R 1 and R 2 are independently from each other and at each occurrence selected from the group consisting of a C 1-10 -alkyl and phenyl;

C 1-10 -alkyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen and phenyl; and

phenyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen and C 1-6 -alkyl.

11. The polymer of claim 1 , wherein:

at least one of m and p is not 0;

R 1 and R 2 area C 1-6 -alkyl; and

C 1-6 -alkyl can be substituted with 1 to 3 of a halogen.

12. The polymer of claim 1 , which is a copolymer comprising:

at least one unit of formula (1):

and at least one unit of formula (10):

wherein:

n is 0 or 1;

m and p are independently from each other 0, 1, 2, 3, 4, 5 or 6,

provided that the sum of n, m and p is at least 2, and n and p are not 0 at the same time;

q is 0, 1, 2, 3, 4, 5 or 6;

Ar 1 , Ar 2 and Ar 3 are independently from each other a C 6-14 -arylene or a C 6-14 -aryl, which may be substituted with 1 to 4 substituents independently selected from the group consisting of a C 1-30 -alkyl, a C 2-30 -alkenyl, a C 2-30 -alkynyl, a C 5-8 -cycloalkyl, a C 6-14 -aryl and a 5 to 14 membered heteroaryl;

X 1 , X 2 , X 3 , and X 4 are independently from each other and at each occurrence O or S;

R 1 , R 2 and R 3 are independently from each other and at each occurrence selected from the group consisting of a C 1-30 -alkyl, a C 2-30 -alkenyl, a C 2-30 -alkynyl, a C 5-8 -cycloalkyl, a C 6-14 -aryl and a 5 to 14 membered heteroaryl;

C 1-30 -alkyl, C 2-30 -alkenyl and C 2-30 -alkynyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 5-6 -cycloalkyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl;

C 5-8 -cycloalkyl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 1-10 -alkyl, a C 2-10 -alkenyl, a C 2-10 -alkynyl, a C 6-10 -aryl and a 5 to 10 membered heteroaryl; and

C 6-14 -aryl and 5 to 14 membered heteroaryl can be substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, CN, a C 1-10 -alkyl, a C 2-10 -alkenyl, a C 2-10 -alkynyl and a C 5-6 -cycloalkyl.

13. A composition, comprising:

the polymer of claim 1 and a solvent.

14. The composition of claim 13 , further comprising:

a crosslinker.

15. A process for preparing an electronic device containing a layer formed from the composition of claim 13 , the process comprising:

applying the composition on a pre-cursor of the electronic device in order to form the layer.

16. An electronic device obtained by the process of claim 15 .

17. An article, comprising:

the polymer of claim 1 ,

wherein the article is selected from the group consisting of a dielectric layer, a resist layer, an insulating layer, a passivation layer, a planarization layer, an encapsulation layer and a coating layer.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2020
From: BASF SE
To: CLAP CO., LTD.
Reel/Frame 052459/0201 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 16, 2018
From: BASF SCHWEIZ AG
To: BASF SE
Reel/Frame 045823/0202 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 16, 2018
From: BASF SOUTH EAST ASIA PTE. LTD.
To: BASF SE
Reel/Frame 045823/0211 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 14, 2018
From: KAELBLEIN, DANIEL; WU, CHAO; KNOLL, KONRAD; KOPPING, JORDAN THOMAS
To: BASF SE
Reel/Frame 045207/0048 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 14, 2018
From: BRUNETTI, FULVIO G.; ZHOU, MI; BECKER, STEFAN; PRAPTANA, RAIMOND
To: BASF SOUTH EAST ASIA PTE. LTD.
Reel/Frame 045207/0054 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 14, 2018
From: MARTIN, EMMANUEL
To: BASF SCHWEIZ AG
Reel/Frame 045207/0084 →
Priority Claims (1)
EP 14186306 · Sep 25, 2014 · regional
Continuity (1)
Related Publication 20170250358A1 · Aug 31, 2017